Trifluoroacetic acid → (3R,7R)-3-Amino-1-(cyclopropylmethyl)-7-phenylazepan-2-one

Participants

Reaction Steps

Trifluoroacetic acid (2.5 mL) was added to a solution tert-butyl (3R,7R)-1-(cyclopropylmethyl)-2-oxo-7-phenylazepan-3-ylcarbamate (82 mg, 0.23 mmol) in dichloromethane (5 mL). After 1 h, the mixture was concentrated and aqueous saturated sodium bicarbonate was added. The mixture was extracted with dichloromethane (2×), and the combined organic extracts were dried over magnesium sulfate, filtered, and concentrated to give the title compound (53 mg). 1H NMR (500 MHz, CDCl3) □ 7.40-7.37 (m, 2H), 7.34-7.31 (m, 3H), 4.97 (dd, J=9.3, 3.7 Hz, 1H), 4.05 (dd, J=9.8, 4.2 Hz, 1H), 3.24 (dd, J=14.4, 7.1 Hz, 1H), 2.69 (dd, J=14.2, 7.1 Hz, 1H), 2.16-2.10 (m, 2H), 2.03-1.97 (m, 1H), 1.92-1.85 (m, 2H), 1.65-1.56 (m, 1H), 0.69-0.63 (m, 1H), 0.34-0.23 (m, 2H), 0.09-0.04 (m, 1H), −0.10-0.15 (m, 1H).

Provenance & Evidence